Obama Leader on why Veterans Day is Every Day

Jonathan Pride has always been a person dedicated to helping others, following in his father’s and brother’s footsteps in the military. But it was a moment of storytelling, and vulnerability, during his Obama Leaders program that would lead him to his biggest act of service.

That catharsis pushed him to found the Caterpillar Leadership Institute, which develops leaders by helping them share their stories, even as Pride also worked as the chief student success officer at NPower, a national nonprofit that creates opportunities in tech for young adults and military-connected individuals from low- and moderate-income communities.

Based in Fort Worth, Texas, Pride is a 2024-2025 Obama Foundation USA Leader who previously served as an Army intelligence officer and combat veteran. 

He said every time he sees transformation in someone’s life, it refills him “twofold, tenfold, 100-fold. I wanted other people to have the opportunities I’ve had, because growing up, I didn’t have them.” 

His path began with his father, Willie Dan Pride, a Korean War veteran who was 52 when Pride was born. Willie Pride served in a segregated military, but he encouraged both of his sons to enlist. Pride’s older brother, Matthew, graduated from West Point and plans to retire next year as a Lieutenant Colonel. Jonathan went the ROTC path and received his commission from Norwich University and served eight years in the Army.

Pride spent his early career inspired by his father’s vision and his brother’s example. His assignments included serving as a general’s aide at the Operational Test Command in Fort Hood, Texas. Over the years, he saw soldiers he had mentored earn promotions and he realized he was a natural coach: “Leadership is the ability to impact and influence others for good. That’s my mission.” 

The Caterpillar Institute grew from Pride’s experience in The Obama Foundation’s Leaders USA program. During the cohort’s storytelling exercise, Pride shared about his father, a story he had never shared, not even at his funeral—a story of discovering that true leadership and his father’s legacy are defined not by status, but by the ordinary acts of care that transform a community and create lasting impact.

“I had a soul cry realizing so many other leaders from my cohort experienced a similar experience. That’s when I knew it was time to launch into my calling,” Pride said.

He founded the institute soon after, built on four interconnected pillars: storytelling, ownership, abundance, and resilience. Participants begin with a leadership assessment and work through programs called “leadership response labs,” modeled on his own military training. Each lab is designed to support leadership development in a practical, applicable, and effective way. 

“We’re all caterpillars, and we all have a cocoon, but we don’t have to go anywhere to find our wings,” Pride said with a smile. “They’re already within us.”

Pride said Veterans Day honors more than those in uniform; it recognizes military families too. His wife managed their household through 30-day field exercises and a six-month absence, with a toddler and an infant at home. His mother prayed nightly for two sons deployed to Iraq at the same time.

“Veterans Day to me means just saying thank you, not only to the people who served but to the community who served with us,” Pride said.

He acts on that year-round. Pride said he connects every veteran he meets with disability and mental health resources, and he shares his own experience, saying, “I’ve done it. I’ve gone through it. It’s okay to not have it together. Just control what you can control and grow into the rest”

Service, he said, outlasts the uniform.

“Your service is lifelong, and our country’s commitment to you is also lifelong,” Pride shared.